PLANAR CHIRAL ARENE TRICARBONYLCHROMIUM COMPLEXES VIA ENANTIOSELECTIVE DEPROTONATION ELECTROPHILE ADDITION-REACTIONS

Authors
KUNDIG EP QUATTROPANI A
Citation
Ep. Kundig et A. Quattropani, PLANAR CHIRAL ARENE TRICARBONYLCHROMIUM COMPLEXES VIA ENANTIOSELECTIVE DEPROTONATION ELECTROPHILE ADDITION-REACTIONS, Tetrahedron letters, 35(21), 1994, pp. 3497-3500
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
21
Year of publication
1994
Pages
3497 - 3500
Database
ISI
SICI code
0040-4039(1994)35:21<3497:PCATCV>2.0.ZU;2-L
Abstract
Sequential reaction of prochiral (eta(6)-arene(Cr(CO)(3) complexes wit h chiral amide bases and electrophiles yielded planar chiral complexes . Benzaldehyde acetal and phenyl carbamate complexes gave O-substitute d products with 64 to 81% enantiomeric excess. With the benzaldehyde a cetal complex, competitive benzylic deprotonation occured. Enantiomeri c purity of the substituted carbamate complexes could be increased to >90% ee by fractional crystallization. The racemate crystallized selec tively, leaving the enantiomerically enriched complex in solution.